CN100548284C - A kind of microemulsion of hypocrellin and preparation method thereof - Google Patents
A kind of microemulsion of hypocrellin and preparation method thereof Download PDFInfo
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- CN100548284C CN100548284C CNB2006100016772A CN200610001677A CN100548284C CN 100548284 C CN100548284 C CN 100548284C CN B2006100016772 A CNB2006100016772 A CN B2006100016772A CN 200610001677 A CN200610001677 A CN 200610001677A CN 100548284 C CN100548284 C CN 100548284C
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Abstract
The invention discloses a kind of microemulsion of hypocrellin and preparation method thereof.Microemulsion of hypocrellin provided by the present invention contains the component of following weight portion: hypocrellin 0.01-0.07, natural oil 4-10, surfactant 2.2-10, water-soluble polyol 2-5, water 85-97.The present invention utilizes natural oil, surfactant to be encapsulating material, fat-soluble hypocrellin is sealed made microemulsion, and its particle diameter is suitable for intravenous injection at 20-100nm; It is high that resulting microemulsion of hypocrellin has stability, targeting and biodegradability are good, the characteristics that kept hypocrellin class photosensitizer high light power function simultaneously, available water, normal saline, phosphate buffer are diluted to specific concentrations, are mixed with the intravenous injection injection of hypocrellin medicine easily.Microemulsion of hypocrellin raw material of the present invention is cheap and easy to get, preparation method is simple, easy to operate, preparation technology's cost is low, is easy to realize industrialization, have a extensive future.
Description
Technical field
The present invention relates to a kind of microemulsion of hypocrellin and preparation method thereof.
Background technology
Hypocrellin, it is the natural phytochrome of a class that from a kind of parasitical fungi-Hypocrella bambusae (Bet Br). Sace (Hypocrellabambusae (B.et Br.) Sacc.) of special product on the Yunnan Province of China Fargesia, extracts, feature with desirable photosensitizer such as singlet oxygen quantum yield height, structure are clear and definite, good, the dark toxicity of chemical modification is low, internal metabolism is fast generally acknowledges it is the most promising a kind of novel smooth power photosensitizer.Among the people once with hypocrellin treatment stomachache and arthritis, dermatosis; Now proved in light power anti AIDS virus, antitumor and blood capillary class disease potential use has been arranged.Hypocrellin comprises hypocrellin (HA, formula I structure, molecular formula C
30H
26O
16) and HB Hypocrellin B (HB, formula II structure, molecular formula C
30H
24O
9).
(formula I) (formula II)
The common focus degree of depth of blood capillary class disease is no more than 1 millimeter, conforms to hypocrellin class photosensitizer master absorbing light penetration depth; And, may increase injury on the contrary to the deep layer normal structure with the longwave optical irradiation to the disease of this shallow table type.Therefore, the characteristic of hypocrellin short wavelength absorption is its inferior position (tumor phototherapy window is defined as 600-900nm) for light power medical treatment entity tumor; Medical superficial tumor and blood capillary class disease are then become its special advantages.Blood capillary class disease comprises nevus flammeus, macula retinae degeneration etc., belongs to the commonly encountered diseases category, and photodynamic therapy is the first-selected therapy of this type of disease of treatment at present.Owing to the similar features of focus, can be extended to the light power medical treatment of diseases such as joint sheath class disease, superficial tumor, infantile tumour, the remaining tumor of postoperative such as rheumatoid easily.
The medicine of blood capillary class disease is by in the intravenous injection input body, and hypocrellin is the fat-soluble organic molecule of a class, can spontaneous gathering in polar solvent and blood and form capillary embolism; And the soluble derivative that obtains by chemical modification the cellular uptake rate is low and reduce greatly even lose biological photodynamic activity in vivo.Therefore, the microvascular disease photo-dynamical medicine must satisfy the smooth transmission in blood and select the double requirements of absorption on focus.Because the hypocrellin parent has very high photosensitization efficient, and its photophysical property is well positioned to meet the requirement of the light power medical treatment of blood capillary class disease, therefore can directly adopt biocompatible materials and fat-soluble hypocrellin molecule to assemble the physicochemical properties of improving medicine, thereby satisfy the requirement of clinical photo-dynamical medicine with amphipathic characteristic.In order to reach this target, hypocrellin-micelle, liposomal systems have been carried out a large amount of research, obtained important progress.But also exist many problems, can have advantages of higher stability, lack problems such as target body cell selective and parents' material biocompatibility but have as micelle volume; Liposome has very high targeting and drug release characteristics, but belongs to viscid Liposomal formulation poor stability, leaks fast, perishable.
Microemulsion is a kind of water that contains, the single phase property Thermodynamically stable solution of oil and the amphiphilic material of fat water, this solution as far back as nineteen forty-three by (T.P.Hoar such as Hoar, J.H.Schulman, Transparent water-in-oildispersions:the oleopathic hydro-micelle, Nature 152 (1943) 102-103) obtain by obtaining a kind of transparent single phase soln with hexanol titration emulsion, people such as nineteen fifty-nine Schulman is with (J.H.Schulman then, W.Stoeckenius, L.M.Prince, Mechanism offormation and structureof micro emulsions by electronmicroscopy, J.Phys.Chem.63 (1959) 1677-1680) this solution called after microemulsion that obtains.Microemulsion has ultralow oil water interfacial tension, and not phase-splitting does not precipitate, and is transparent or semitransparent thermodynamic stable system, can improve drug capacity with microemulsion as pharmaceutical carrier; Reduce medicine and improve medicine stability with extraneous contacting; Similar with the composition and the size of low density lipoprotein, LDL in the human plasma (LDL), can reduce reticuloendothelial picked-up and liver metabolism, improve drug effect.
Summary of the invention
The purpose of this invention is to provide a kind of microemulsion of hypocrellin and preparation method thereof with good light power performance.
Microemulsion of hypocrellin provided by the present invention, contain the component of following weight portion:
Hypocrellin 0.01-0.07,
Natural oil 4-10,
Surfactant 2.2-10,
Water-soluble polyol 2-5,
Water 85-97.
Here, hypocrellin can be selected hypocrellin or HB Hypocrellin B for use.
Natural oil can be selected from one or more in Squalene, Flos Camelliae Japonicae seed oil, Macadamia ternifolia oil, Semen Maydis oil, olive oil, Oleum Brassicae campestris, Oleum sesami, Semen Tritici aestivi germ oil, Flos Camelliae Japonicae caul-fat, Oleum Ricini, safranine caul-fat, Oleum Gossypii semen, soybean oil, Oleum Arachidis hypogaeae semen and the Oleum Hippophae.
Optional in tween 20, Tween-40, Tween-60, tween 80, Arlacel-60, Arlacel-65, Arlacel-80, Arlacel-85, poloxamer 188, polyvinylpyrrolidone, Polyethylene Glycol, isopropyl myristate, OP, Brij 35, Semen sojae atricolor ovum phosphoric acid and Ovum Gallus domesticus Flavus lecithin one or more of surfactant.
Water-soluble polyol is selected from one or more in propylene glycol, glycerol, two glycerol, polyglycereol, polyglycerin ester and the Sorbitol.
This microemulsion of hypocrellin can adopt following dual mode to be prepared:
Method one is that 0.01-0.07 weight portion hypocrellin, 4-10 weight portion natural oil, 2.2-10 weight portion surfactant are mixed, and stirs then down to add 2-5 weight portion water-soluble polyol and 85-97 weight parts water, continues to stir to obtain colostric fluid; With gained colostric fluid sonic oscillation, obtain described microemulsion of hypocrellin.
Method two, be that 0.01-0.07 weight portion hypocrellin, 4-10 weight portion natural oil, 2.2-10 weight portion surfactant are mixed, dissolve with 75-85 weight fraction chloroform, the evaporation chloroform becomes skim, dry up the back and add 2-5 weight portion water-soluble polyol and 85-97 weight parts water, stir and obtain colostric fluid; With gained colostric fluid sonic oscillation, obtain described microemulsion of hypocrellin.
The present invention utilizes natural oil, surfactant to be encapsulating material, fat-soluble hypocrellin is sealed made microemulsion, and its particle diameter is suitable for intravenous injection at 20-100nm; It is high that resulting microemulsion of hypocrellin has stability, targeting and biodegradability are good, the characteristics that kept hypocrellin class photosensitizer high light power function simultaneously, available water, normal saline, phosphate buffer are diluted to specific concentrations, are mixed with the intravenous injection injection of hypocrellin medicine easily.Microemulsion of hypocrellin raw material of the present invention is cheap and easy to get, preparation method is simple, easy to operate, preparation technology's cost is low, is easy to realize industrialization, have a extensive future.
Description of drawings
Fig. 1 is the absorption spectrum of embodiment 1 HB Hypocrellin B microemulsion;
Fig. 2 is the fluorescence emission spectrum of embodiment 1 HB Hypocrellin B microemulsion;
Fig. 3 is the particle size distribution figure of embodiment 1 HB Hypocrellin B microemulsion.
The specific embodiment
Embodiment 1,
2mg HB Hypocrellin B (HB) adds the 200mg Ovum Gallus domesticus Flavus lecithin, 200mg Oleum Glycines, the 100mg tween 80 places the pyriform bottle, 40 ℃ of water-baths are stirred down and are made mix homogeneously, keep stirring down, slowly add 0.27M glycerine water solution 3.41mL, continue to stir and get colostrum half an hour, the gained colostrum places ice-water bath with sonde-type Ultrasound Instrument in 80w ultrasonic 1 hour, get HB Hypocrellin B microemulsion 4mL, do to fill nitrogen seal device in 4 ℃ of cold preservations of refrigerator after sterilization filter (0.22 μ m is selected in the aperture for use) sterilization with microporous membrane.
Embodiment 2,
2mg hypocrellin (HA) adds the 200mg soybean lecithin, the 200mg olive oil, the 100mg Tween-60 places the pyriform bottle, 40 ℃ of water-baths are stirred down and are made mix homogeneously, keep stirring down, slowly add 0.27M glycerine water solution 3.41mL, continue to stir and get colostrum half an hour, the gained colostrum places ice-water bath with sonde-type Ultrasound Instrument in 80w ultrasonic 1 hour, get hypocrellin microemulsion 4mL, do to fill nitrogen seal device in 4 ℃ of cold preservations of refrigerator after sterilization filter (0.22 μ m is selected in the aperture for use) sterilization with microporous membrane.
Embodiment 3,
2.8mg HB Hypocrellin B (HB), the 200mg Ovum Gallus domesticus Flavus lecithin, the 200mg Oleum Hippophae, 100mg poloxamer 188 places the pyriform bottle, add the 1mL chloroform dissolve red solution, 50 ℃ of water-bath rotary evaporations become skim half an hour, argon dries up, stir and slowly add 0.2M two glycerine water solution 3.41mL down, continue to stir and get colostrum half an hour, the gained colostrum places ice-water bath with sonde-type Ultrasound Instrument in 80w ultrasonic 1 hour, get HB Hypocrellin B microemulsion 4mL, do to fill nitrogen seal device in 4 ℃ of cold preservations of refrigerator after sterilization filter (0.22 μ m is selected in the aperture for use) sterilization with microporous membrane.
Embodiment 4,
0.7mg HB Hypocrellin B (HB), the 12mg soybean lecithin, the 100mg Oleum Hippophae, 10mg Brij 35 places the pyriform bottle, add the 1mL chloroform dissolve red solution, 50 ℃ of water-bath rotary evaporations become skim half an hour, argon dries up, add a small amount of 0.27M glycerine water solution on the thin film and make its moistening, powerful then the stirring down adds the 0.27M glycerine water solution to 1mL, get colostrum after half an hour, the gained colostrum places ice-water bath with sonde-type Ultrasound Instrument in 80w ultrasonic 1 hour, get HB Hypocrellin B microemulsion 1mL, do to fill nitrogen seal device in 4 ℃ of cold preservations of refrigerator after sterilization filter (0.22 μ m is selected in the aperture for use) sterilization with microporous membrane.
Embodiment 5,
0.5mg HB Hypocrellin B (HB), 40mg OP, 60mg Flos Camelliae Japonicae seed oil, 5mg Arlacel-65 place the pyriform bottle, 40 ℃ of water-baths are stirred down and are made mix homogeneously, keep stirring down, slowly add the 0.27M glycerine water solution to 1mL, continue to stir and get colostrum half an hour, the gained colostrum places ice-water bath with sonde-type Ultrasound Instrument in 80w ultrasonic 1 hour, get HB Hypocrellin B microemulsion 1mL, do to fill nitrogen seal device in 4 ℃ of cold preservations of refrigerator after sterilization filter (0.22 μ m is selected in the aperture for use) sterilization with microporous membrane.
Embodiment 6,
2mg hypocrellin (HA) adds the 200mg soybean lecithin, 200mg Oleum Glycines, the 100mg isopropyl myristate places the pyriform bottle, 40 ℃ of water-baths are stirred down and are made mix homogeneously, keep stirring down, slowly add 0.27M polyglycerin ester aqueous solution 3.41mL, continue to stir and get colostrum half an hour, the gained colostrum places ice-water bath with sonde-type Ultrasound Instrument in 80w ultrasonic 1 hour, get hypocrellin microemulsion 4mL, do to fill nitrogen seal device in 4 ℃ of cold preservations of refrigerator after sterilization filter (0.22 μ m is selected in the aperture for use) sterilization with microporous membrane.
Embodiment 7,
2.8mg hypocrellin (HA) adds the 200mg Ovum Gallus domesticus Flavus lecithin, 200mg Oleum Glycines, the 50mg tween 80,50mg poloxamer 188 places the pyriform bottle, add the 2mL chloroform dissolve red solution, 50 ℃ of water-bath rotary evaporations become skim half an hour, argon dries up, stir and slowly add 0.27M aqueous solution of propylene glycol 3.41mL down, continue to stir and get colostrum half an hour, the gained colostrum places ice-water bath with sonde-type Ultrasound Instrument in 80w ultrasonic 1 hour, HB Hypocrellin B microemulsion 4mL, do to fill nitrogen seal device in 4 ℃ of cold preservations of refrigerator after sterilization filter (0.22 μ m is selected in the aperture for use) sterilization with microporous membrane.
The sign of embodiment 8, microemulsion of hypocrellin
The photophysical property of microemulsion of hypocrellin of the present invention characterizes with absorption, fluorescence spectrum and fluorescence quantum yield; The type looks of nanoparticle characterize with dynamic light scattering.
With embodiment 1 gained HB Hypocrellin B microemulsion thin up, making HB Hypocrellin B (HB) concentration wherein is 10
-5M measures then.
1, spectroscopic assay
The absorption spectrum of HB Hypocrellin B microemulsion and fluorescence emission spectrogram are respectively as depicted in figs. 1 and 2, the result shows, the absorption spectrum of the hypocrellin in microemulsion and its similar in liposome, micelle, protein molecular microenvironment, the absorption spectrum basic configuration is similar in organic solvent to free hypocrellin, 465nm place absorption intensity does not have too big variation, long wave place absorption value increases to some extent, has reflected the weak interaction feature between photosensitizer molecule and lipid, surface active molecules or the albumen microenvironment; Hypocrellin fluorescence spectrum shape in the microemulsion is compared with the free hypocrellin molecule in being dissolved in organic solvent, and basic identical, fluorescent value slightly reduces, and illustrates that proton type solvent (water) has quenching effect to the fluorescence of hypocrellin.
(2) grain diameter measurement of microemulsion of hypocrellin
It is 10 that sample is made HB Hypocrellin B (HB) concentration wherein with distilled water diluting
-5M gets 3mL and places in the dynamic light scattering (BI-90Plus, Brookhaven Instruments Corporation make), the result as shown in Figure 3, the microemulsion of hypocrellin particle diameter is in the 20-100nm scope.
The light power function experiment of embodiment 9, microemulsion of hypocrellin
The test cell line measurement result: the human umbilical vein endothelial cell of In vitro culture (ECV304), by 8.0 * 10
4The cell density of individual/ml is inoculated in 96 porocyte culture plates, hatch 24 hours after, add photosensitizer, continue to hatch endotheliocyte after 2 hours, adopt the KTP laser irradiation, wavelength is 532nm, the energy density of laser irradiation is 20J/cm
2(power density is 20mw/cm
2), irradiation time is 1000 seconds, adopts the method for MTT thereafter, measures the optical density value in each hole, calculates the cell killing rate.Repeat 3 times, average.Wherein photosensitizer is HB Hypocrellin B liposome and HB Hypocrellin B microemulsion, respectively at the variable concentrations point measurement, gets separately the half amount of killing and wounding and lists in table 1.
Table 1 endotheliocyte OD value and HB are to its kill rate
Annotate: wherein sample 1 is HB Hypocrellin B Liposomal formulation concentration 1000ng/mL, and (Zou Wei, quiet instrument, Jiang Lijin, the hypocrellin photodynamics in liposome solutions is studied, and Chinese science B collects, 26 the 3rd phases of volume, 206-213) preparation to press document; Sample 2 is HB Hypocrellin B microemulsion 300ng/mL, for embodiment 1 prepared; Blank group OD meansigma methods is respectively 0.637,0.6032 fully; Background group OD meansigma methods is respectively 0.0908,0.0942.
The cell killing rate is as shown in the formula obtaining:
Cell killing rate (%)=1-cell survival rate=1-(experimental group OD-background group OD)/(blank fully group OD-background group OD) * 100%
HB Hypocrellin B-liposomal systems successfully has been used for the research (Gu Ying etc. of blood capillary class disease (nevus flammeus, macula retinae degeneration etc.) light power medical treatment, number of patent application: 02116879.2.), be that the contrast experiment of subject cell proves with the blood vessel cell: hypocrellin-liposome is higher tens times than hematoporphyrin derivative photosensitizer to the kill rate of blood vessel cell.And from the median lethal dose(LD 50) of this experiment, HB Hypocrellin B microemulsion of the present invention has higher efficient than HB Hypocrellin B liposome.
Because microemulsion Thermodynamically stable, isotropism, microemulsion of the present invention can be preserved the longer time, can reach more than 6 months; In addition, microemulsion particle diameter of the present invention can not filter through hyperfiltration process degerming method (filtering＞the 200nm composition) between the 20-100 nanometer, can use the heat sterilization method to remove and degerm.Therefore microemulsion of hypocrellin of the present invention can be used for the hypocrellin class medicine intravenous injection injection of the clinical optical dynamic therapy of blood vessel kind disease (maybe needing the disease by intravenous administration).
The preparation-obtained microemulsion of other embodiment also has identical performance, and particle diameter is little, light power curative effect height.
Claims (3)
1, a kind of microemulsion of hypocrellin, contain the component of following weight portion:
Hypocrellin 0.01-0.07,
Natural oil 4-10,
Surfactant 2.2-10,
Water-soluble polyol 2-5,
Water 85-97;
Wherein, described hypocrellin is hypocrellin or HB Hypocrellin B; Described natural oil is selected from a kind of in Flos Camelliae Japonicae seed oil, olive oil, soybean oil and the Oleum Hippophae; Described surfactant is selected from several in Tween-60, tween 80, Arlacel-65, poloxamer 188, polyvinylpyrrolidone, Polyethylene Glycol, isopropyl myristate, OP, Brij 35, soybean lecithin and the Ovum Gallus domesticus Flavus lecithin; Described water-soluble polyol is selected from a kind of in propylene glycol, glycerol, two glycerol and the polyglycerin ester.
2, the preparation method of the described microemulsion of hypocrellin of claim 1, be that 0.01-0.07 weight portion hypocrellin, 4-10 weight portion natural oil, 2.2-10 weight portion surfactant are mixed, stir adding 2-5 weight portion water-soluble polyol and 85-97 weight parts water down then, continue stirring and obtain colostric fluid; With gained colostric fluid sonic oscillation, obtain described microemulsion of hypocrellin; Described hypocrellin is hypocrellin or HB Hypocrellin B; Described natural oil is selected from a kind of in Flos Camelliae Japonicae seed oil, olive oil, soybean oil and the Oleum Hippophae; Described surfactant is selected from several in Tween-60, tween 80, Arlacel-65, poloxamer 188, polyvinylpyrrolidone, Polyethylene Glycol, isopropyl myristate, OP, Brij 35, soybean lecithin and the Ovum Gallus domesticus Flavus lecithin; Described water-soluble polyol is selected from a kind of in propylene glycol, glycerol, two glycerol and the polyglycerin ester.
3, the preparation method of the described microemulsion of hypocrellin of claim 1, be that 0.01-0.07 weight portion hypocrellin, 4-10 weight portion natural oil, 2.2-10 weight portion surfactant are mixed, dissolve with 75-85 weight fraction chloroform, the evaporation chloroform becomes skim, dry up the back and add 2-5 weight portion water-soluble polyol and 85-97 weight parts water, stir and obtain colostric fluid; With gained colostric fluid sonic oscillation, obtain described microemulsion of hypocrellin; Described hypocrellin is hypocrellin or HB Hypocrellin B; Described natural oil is selected from a kind of in Flos Camelliae Japonicae seed oil, olive oil, soybean oil and the Oleum Hippophae; Described surfactant is selected from several in Tween-60, tween 80, Arlacel-65, poloxamer 188, polyvinylpyrrolidone, Polyethylene Glycol, isopropyl myristate, OP, Brij 35, soybean lecithin and the Ovum Gallus domesticus Flavus lecithin; Described water-soluble polyol is selected from a kind of in propylene glycol, glycerol, two glycerol and the polyglycerin ester.
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| CN105561306A (en) * | 2015-01-16 | 2016-05-11 | 南京大学 | Composition containing singlet oxygen protective agent and preparation method thereof |
| PL3225112T3 (en) * | 2016-04-01 | 2022-01-03 | Trioptotec Gmbh | Photosensitiser dispersion and use of the same |
| CN107875038B (en) * | 2017-11-15 | 2021-02-05 | 扬州市职业大学 | Olive oil microemulsion preparation and application thereof as whitening sunscreen agent |
| CN110025785A (en) * | 2019-05-31 | 2019-07-19 | 温州医科大学附属第二医院、温州医科大学附属育英儿童医院 | Hypocrellin A is preparing the application in optical dynamic therapy skin candida albicans infection disease medicament |
| CN113424913A (en) * | 2021-07-15 | 2021-09-24 | 吉林大学 | Preparation method of hypocrellin nano bactericidal emulsion as natural photosensitizer |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1183215A (en) * | 1996-11-22 | 1998-06-03 | 中国科学院生物物理研究所 | Bio-insecticide contg. hypocrelline A and its preparing process |
| CN1389110A (en) * | 2002-05-10 | 2003-01-08 | 张红雨 | Photosensitive biological germicide of perylene quinone and its prepn. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1183215A (en) * | 1996-11-22 | 1998-06-03 | 中国科学院生物物理研究所 | Bio-insecticide contg. hypocrelline A and its preparing process |
| CN1389110A (en) * | 2002-05-10 | 2003-01-08 | 张红雨 | Photosensitive biological germicide of perylene quinone and its prepn. |
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